For a while now I’ve been saying that the best web series think of themselves as startups, not just side projects. The hustle, the grind, the payoff—phases known all too well amongst the kindred souls of web video creators and entrepreneurs. Fitting then, that one new series would decide to turn the cameras on the latest crop of business ventures all trying to build something from nothing. When you think of it, startups already have everything that makes for a good story—drama, conflict, high stakes and passion.

Trep Life premiered online this past week from Chicago-based creators Scotty Cadenhead and Malachi Leopold, a 12-episode documentary series diving into a number of the city’s budding startups. First up is online restaurant delivery service GrubHub and its founders Matt Maloney and Mike Evans. This isn’t a marketing EPK, and despite any narrator or audible interview questions we’re given a rather candid look at the less than glamorous life at a startup. Maloney’s creative balancing of his personal life and recently added baby, show a human side mostly absent from the pages of TechCrunch.

It’s not the first time we’ve seen a polished doc-style look inside the exposed brick walls. Boulder’s TechStars now has two seasons of its introspective series The Founders and Next New Networks briefly bowed the AMEX-backed Small Business Rules back in 2009.

Episode 2 of Trep Life will feature designer Lara Miller, followed soon after by Eboo Patel and Howard Tullman of TRIBECA Flashpoint Academy and a slew of Chicagoland startups like crowdSPRING, Redbox, Bright Pink, Interfaith Youth Core, Minimal, Sittercity, Network After Work and Vesta Preferred Realty. While Chicago is the focus of this first batch, a second season however will turn towards east coast startups in NYC, Boston and D.C., and possibly European startup hubs like London and Paris.

The target audience, Cadenhead tells us, is nested in the 18-35 range, both male and female. “We’re breaking through to the younger crowd by taking them out of the classroom and their 9-5’s into the world of entrepreneurship,” added Cadenhead.

“As for networks,” said Cadenhead about possible distribution partners, “we are most certainly reaching out to partners we believe would have the series best interest in mind, allowing it to reach and influence the expected audience numbers. I’m proud to say, we have had great responses from major networks with the premiere episode of GrubHub. I’m looking forward to developing a network partnership in the coming weeks.”

And for the dollar sign junkies, there are a few nuggets in there, like the fact that GrubHub sent nearly $70 million to independent restaurants, that should make the 11-minute episodes worth sticking it out.

Oh and that name? (Not to be confused with office comedy The Temp Life) It comes from a the middle syllable of “entrepreneur,” as in, “You’re totally trepping out right now.”

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